As for my man Stephen, it might make sense for the Sox to re-sign him at some point but I wouldn't do it any time before at least spring training. There's absolutely no hurry here and he would provide above average depth in the infield if he can't find a multi-year deal somewhere else and thus getting the Sox a draft pick in the process. The only part I don't understand in this article is the last sentence of the article, "the Sox are content to let the market form for Drew before they make their pitch, but a two-year deal, perhaps with an option, could be enough for Drew to return. But never, ever bet against Boras." Why in the world would they offer two years and why the fuck would they even think about an option for a third year? We'd be bidding against ourselves and adding years for no reason whatsoever. I'd say that if no one has picked him up on a multi-year deal by a week or two into spring training that we should offer 1-year at between $5 million and his deal from last year (around $9 million). I would say between $5M and $7M would be ideal for a known quantity who can handle Boston (not to be undersold here), field very well, and continue to be a top 10 or so SS. As you saw last year, we needed that with the struggles Middlebrooks had at the start of the season.
I think the one team that would make sense (aside from the Yankees because you can't predict what they're ever going to do) would be the Mets since they would only have to give up a 3rd round pick for him. They haven't been shy about spending money lately, so a 3-year deal for a 31 year old above average SS, would seem like a good fit for them. Otherwise, I have no problem having Xander, Middlebrooks, and Drew filling out the left side of our infield again, as long as we don't overpay or offer multiple years. Plus, I wouldn't have to buy a new Red Sox shirt this year, which would be nice.